Ethanol → [3-(6-Aminopyridin-3-yl)phenyl]methanol

HRID 1891236Notes

Reaction equation

HRID 1891236 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].Br[C:8]1[CH:9]=[CH:10][C:11]([NH2:14])=[N:12][CH:13]=1.[OH:15][CH2:16][C:17]1[CH:18]=[C:19](B(O)O)[CH:20]=[CH:21][CH:22]=1.C(O)C>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:14][C:11]1[N:12]=[CH:13][C:8]([C:21]2[CH:22]=[C:17]([CH2:16][OH:15])[CH:18]=[CH:19][CH:20]=2)=[CH:9][CH:10]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 706222-Amino-5-bromopyridineHCID 2734662[3-(Hydroxymethyl)phenyl]boronic acid

Product 1

HCID 44232377[3-(6-Aminopyridin-3-yl)phenyl]methanolYield 86.2%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

2.0 g of tetrakis(triphenylphosphine)palladium and 75 ml of a 2M solution of sodium carbonate are added to a round-bottomed flask containing a solution of 5.0 g of 5-bromopyridin-2-ylamine in 140 ml of toluene, 5.7 g of 3-(hydroxymethyl)phenylboronic acid and 70 ml of ethanol degassed beforehand. The mixture is heated at 80° C. for 16 h. After cooling, the reaction mixture is concentrated under reduced pressure. The residue is taken up between water and ethyl acetate. The organic phase is separated, dried and concentrated under reduced pressure. The residue is purified by silica gel chromatography, elution being carried out with a dichloromethane/methanol mixture. 4.99 g of compound are obtained.

Workup

  1. temperatureAfter cooling
  2. concentrationthe reaction mixture is concentrated under reduced pressure
  3. customThe organic phase is separated
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is purified by silica gel chromatography, elution

Sources & evidence

ORD record
ord-e1cd0982595a41b5a19da61b6a9c4575
Source dataset
uspto-grants-2013_08
Patent number
US08507520B2

Reaction notes

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